EP1461393A4 - Pigmented hot melt inks - Google Patents
Pigmented hot melt inksInfo
- Publication number
- EP1461393A4 EP1461393A4 EP02796091A EP02796091A EP1461393A4 EP 1461393 A4 EP1461393 A4 EP 1461393A4 EP 02796091 A EP02796091 A EP 02796091A EP 02796091 A EP02796091 A EP 02796091A EP 1461393 A4 EP1461393 A4 EP 1461393A4
- Authority
- EP
- European Patent Office
- Prior art keywords
- hot melt
- melt ink
- ink composition
- vehicle
- pigment
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/30—Inkjet printing inks
- C09D11/34—Hot-melt inks
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/02—Printing inks
- C09D11/12—Printing inks based on waxes or bitumen
Definitions
- Hot melt inks are solid at room temperature and liquid at temperatures above room temperature. Hot melt inks can be used, for example, in digital printing methods. During printing, the ink is heated until it becomes liquid which is then ejected through a printhead onto a substrate. The ink solidifies on the substrate.
- Dyes have usually been preferred for use in hot melt inks, since they completely 10 dissolve in the medium. Unlike pigments, they typically do not settle to the bottom of a reservoir or agglomerate to block the printhead.
- pigments have many advantages over dyes.
- One advantage is that pigments are more heat-stable than dyes. This can be especially important when hot melt inks are heated to an elevated temperature during printing.
- Another advantage is that pigments can be less likely to 15 bleed or sublime than dyes. Therefore, there is a need for pigmented hot melt inks in which pigments are stabilized from settling or agglomerating.
- a hot melt ink composition includes a vehicle, a pigment having a surface including a modifying group, and a polymeric dispersant including a group which associates with the modifying group and a backbone which is miscible with the vehicle.
- a hot melt ink composition in another aspect, includes a vehicle, a pigment 25 . having a volatile content at least 10% (e.g., at least 12%, or in a range of 14% to 22%), and a polymeric dispersant including a group which associates with the pigment and a backbone which is miscible with the vehicle.
- a hot melt ink composition includes a vehicle that has a melting point at a temperature ranging from 50°C to 150°C, a pigment that has a 30 volatile content at least 10% and a modified surface including an oxygen-containing functionality, and a polymeric dispersant that includes a copolymer including a polyamine and a fatty acid.
- a vehicle is the color-carrying medium of the ink.
- the vehicle can include one or more materials such as a wax or resin.
- the vehicle remains in a solid state at the 5 room temperature (20°C to 25 °C) and melts into a liquid state at temperatures above its melting point.
- the melting point of the vehicle can be a temperature ranging from 50°C to 150°C (e.g., from 65°C to 100°C or from 80°C to 90°C).
- a modifying group is a heteroatom-containing group, such as, for example, hydroxyl, carboxyl, ester, ether, amino, amido, or thiol.
- the o modifying group can include an oxygen-containing functionality, such as a carboxyl or phenol group.
- a polymeric dispersant includes a group that associates with the pigment or the modifying group and a backbone that is miscible with the vehicle.
- the polymeric dispersant can assist in stabilizing a pigment in a hot melt ink composition. By 5 stabilizing the pigment, the pigment is less likely to agglomerate or settle in the hot melt ink composition.
- An example of the polymeric dispersant can include a copolymer including a polyamine and a fatty acid.
- the polymeric dispersant has a group that associates with the pigment or the modifying group by, for example, a non- covalent interaction, including a coulombic interaction, a hydrogen-bonding 0 interaction, a hydrophobic interaction, or a Lewis acid-Lewis base interaction.
- a pigment has a volatile content relating to a percentage of oxygen-containing functionalities on the surface of the pigment.
- the oxygen-containing functionalities can include, but are not limited to, carboxyl, phenol, and those contributing to a low pH value.
- a volatile content of a pigment can be measured by heating an unheated mass of 5 a pigment in a sealed crucible to 950°C, and determining the postheated mass of the remaining material in the crucible. The volatile content is calculated as (1 -(postheated mass / unheated mass)) x 100%.
- a process for preparing a hot melt ink composition includes heating the hot melt ink and filtering the heated hot melt ink through a one 0 micron filter.
- a pigmented hot melt ink includes a vehicle, a pigment having a surface including a modifying group, and a dispersant including a group that associates with the modifying group or the pigment and a backbone that is miscible with the vehicle.
- the vehicle may include a wax.
- the wax provides the ink with the property of being solid at the room temperature, but liquid at an elevated temperature.
- the ink can melt between 50°C and 150°C, between 65°C and 100°C, or preferably, between 80°C and 90°C.
- the pigmented hot melt ink should contain enough wax that the ink, as a whole, is a hot melt material.
- the vehicle may also contain a combination of waxes.
- the ink contains about 50% to about 90% by weight wax, e.g., about 55% to about 75% by weight wax.
- waxes include, but are not limited to, stearic acid; succinic acid; beeswax; candelilla wax; carnauba wax; alkylene oxide adducts of alkyl alcohols; phosphate esters of alkyl alcohols; alpha alkyl omega hydroxy poly (oxyethylene); allyl nonanoate; allyl octanoate; allyl sorbate; allyl tiglate; rice bran wax; paraffin wax; microcrystalline wax; synthetic paraffin wax; synthetic paraffin and succinic derivatives; petroleum wax; synthetic petroleum wax; cocoa butter; diacetyl tartaric acid esters of mono and diglycerides; mono and diglycerides; alpha butyl omega hydroxypoly(oxyethylene)poly(oxypropylene); calcium pantothenate; fatty acids; organic esters of fatty acids; calcium salts of fatty acids; mono & diesters of fatty acids; sucrose fatty acid esters; calcium stearol
- the wax can be a beeswax, a carnauba wax, a paraffin wax, a synthetic paraffin wax or a microcrystaline wax.
- the vehicle may include one or more resins.
- the resin provides the ink with a desired viscosity, thermal stability, flexibility, and adhesion properties.
- the ink should include enough resin to achieve the desired viscosity, stability, flexibility, and adhesion.
- the ink contains about 0% to about 50% by weight resin, e.g., about 20% to about 30% by weight resin.
- resins include, but are not limited to, acacia (gum arabic); gum ghatti; guar gum; locust (carob) bean gum; karaya gum (sterculia gum); gum 5 tragacanth; chicle; highly stabilized rosin ester; tall oil; manila copais; corn gluten; coumarone-indene resins; crown gum; damar gum; p, alpha-dimethylstyrene; gum elemi; ethylene oxide polymer and its adducts; ethylene oxide/propylene oxide copolymer and its adducts; galbanum resin; gellan gum; ghatti gum; gluten gum; gualac gum; guarana gum; heptyl paraben; cellulose resins, including methyl and o hydroxypropyl; hydroxypropyl methylcellulose resins; isobutylene-isoprene copolymer; mastic gum; oat gum
- the resin can be a rosin glycerol ester, an ethylene vinyl acetate (EVA), or a 5 poly amide resins.
- the wax preferably, is used as a main component of the vehicle and the resin is used as an additive component thereof.
- the wax can be mixed with other waxes to change the vehicle characteristics, such as its polarity, so that a pigment or a dispersant is more or less soluble in the vehicle, if 0 necessary.
- the pigmented hot melt ink includes a pigment having a modifying group on a surface of the pigment.
- the pigment may be either an organic or inorganic pigment.
- the modifying group can be introduced by, for example, oxidizing the pigment.
- the ink may also contain a combination of pigments.
- the ink contains about 1% to about 35% by weight pigment, e.g., about 3% to about 10% by weight pigment.
- pigments include, but are not limited to, pigment blues (PB) 15, 15:3, 15:4, 16, 22, 28, 64, 68; pigment reds (PR) 3, 4, 48, 81, 97, 113, 122, 175, 202, 217; pigment yellows (PY) 2, 7, 53, 111, 155, 151, 175, 194; pigment blacks 7, carbon black, graphite; and pigment white titanium dioxide.
- PB pigment blues
- PR pigment reds
- PY pigment yellows
- the pigment can be a carbon black pigment.
- the carbon black pigment may have a surface including a modifying group, such as an oxygen-containing functionality (e.g., a carboxyl or phenol group).
- a volatile content of the carbon black pigment can be at least 10%, at least 12%, or in a range of 14% to 22%.
- the pigmented hot melt ink also includes a polymeric dispersant including a group that associates with the modifying group or the pigment and a backbone that is miscible with the vehicle described above.
- the polymeric dispersant can assist in stabilizing the pigment in the hot melt ink.
- the dispersant can, for example, prevent agglomeration of the pigment.
- the ink can include between about 1% and 10% by weight dispersant, e.g., about 3% and 8% by weight dispersant.
- dispersants include, but are not limited to, Solsperse 13,650, 13,940, 17,000; Byk 108; Tego Dispers 700; UNIQEMA 5543; and EFKA 5244, 5207, 6750; which are all commercially available from Avecia; Byk Chemie; Tego Chemie; Zephryn Uniquema; and EFKA additives, respectively.
- the dispersant can be a co-polymer including a polyamine and a fatty acid, such as Solsperse 13,650.
- the selection of the dispersant depends on an ink composition including a vehicle and a pigment.
- the selected dispersant can be soluble in the vehicle, can lack of volatility at an elevated temperature (e.g., 120°C), and can have good affinity for the pigment.
- the dispersant can also include a synergist that aids dispersion.
- An example of a suitable synergist is a substituted ammonium phthalocyanine such as Solsperse 5,000.
- the pigmented hot melt ink may include other conventional hot melt ink ingredients such as stabilizers, oils, flexibilizers, plasticizers, and other additives.
- Stabilizers can inhibit oxidation of the ink.
- Oils, flexibilizers, and plasticizers can reduce the viscosity of the ink.
- stabilizers, oils, flexibilizers and plasticizers include, but are not limited to, butylated hydroxyanisole (BHA); butylated hydoxytoluene (BHT); propyl gallate; tert-butyl hydroquinone (TBHQ); ethylenediaminetetraacetic acid (EDTA); methyl paraben; propyl paraben; benzoic acid; glycerin; lecithin and modified lecithins; agar-agar; dextrin; diacetyl; enzyme modified fats; glucono delta-lactone; carrot oil; chincona extract; rapeseed oil; pectins; propylene glycol; peanut oil; sorbitol; acetophenone; brominated vegetable oil; polyoxyethylene 60 sorbitan mono stearate; olestra; castor oil; oiticia oil; 1,3 butylene glycol; coconut oil and its derivatives; corn oil; substitute
- a pigmented hot melt ink can be prepared by a method that is also within the scope of this invention.
- the method includes combining all of the ink ingredients except for a resin; heating the resulting combination to a temperature above its melting point and milling; mixing the resin with the liquified combination; and filtering the mixture through a 1 ⁇ m filter.
- the hot melt ink can be used with a conventional hot melt ink jet printer, such as a MARKEM model 5000 inkjet printer.
- a hot melt ink was prepared as follows: Beeswax was loaded into a heated flask. A dispersant, parts indicated in Table 1, was added with stirring. A pigment, 4 parts by weight, was added slowly with stirring. The resulting solution was mixed using a Cowles type blade at 1000 rpm for one hour to wet and pre-disperse the pigment. The solution was then loaded into a horizontal media mill, grounded at 2000 rpm for 2 hours at 120°C, and removed from the mill. A resin, rosin ester resin, 24 parts by weight, was mixed with the solution with light stirring. The mixture was then filtered through a one micron glass fiber filter. Note that the beeswax was made up the rest of 100 parts.
- the stability of the ink was tested by placing the test ink in a test tube which was placed into an oven at 120°C. Ink remained undisturbed for up to 4 weeks. At that point ink was evaluated for the presence of a lighter shade or clear fluid on top surface of ink sample. The bottom of the ink sample was evaluated for any signs of pigment settling, agglomeration or increased concentration of pigment relative to top of sample. Samples were also evaluated for change in particle size by optical microscopy. Stable samples show little if any change in pigment concentration from top of sample to bottom and no discernable change in particle size under the optical microscope. Non- stable samples show large changes and usually display a clear fluid at the top of the test tube.
- pigmented hot melt inks of this invention were on average 25% more optically dense (bolder) than their dye-based counterparts.
- Table 1 Stability test on pig: mented hot melt inks.
Abstract
Description
Claims
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US10/032,132 US6702884B2 (en) | 2001-12-31 | 2001-12-31 | Pigmented hot melt inks |
US32132 | 2001-12-31 | ||
PCT/US2002/041560 WO2003057788A1 (en) | 2001-12-31 | 2002-12-27 | Pigmented hot melt inks |
Publications (3)
Publication Number | Publication Date |
---|---|
EP1461393A1 EP1461393A1 (en) | 2004-09-29 |
EP1461393A4 true EP1461393A4 (en) | 2005-03-16 |
EP1461393B1 EP1461393B1 (en) | 2011-02-09 |
Family
ID=21863271
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP02796091A Expired - Lifetime EP1461393B1 (en) | 2001-12-31 | 2002-12-27 | Pigmented hot melt inks |
Country Status (5)
Country | Link |
---|---|
US (1) | US6702884B2 (en) |
EP (1) | EP1461393B1 (en) |
AU (1) | AU2002360809A1 (en) |
DE (1) | DE60239157D1 (en) |
WO (1) | WO2003057788A1 (en) |
Families Citing this family (27)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7347892B2 (en) * | 2004-08-13 | 2008-03-25 | Xerox Corporation | Phase change inks containing modified pigment particles |
EP2003982B1 (en) | 2006-03-29 | 2020-12-09 | Wm. Wrigley Jr. Company | Non-contact printed comestible products and apparatus and method for producing same |
JP4936826B2 (en) * | 2006-09-04 | 2012-05-23 | 株式会社サクラクレパス | Crayon and its manufacturing method |
US20080098927A1 (en) * | 2006-10-26 | 2008-05-01 | Xerox Corporation | Pigmented phase change inks |
US20080221543A1 (en) * | 2007-03-06 | 2008-09-11 | Todd Wilkes | Disposable absorbent product having a graphic indicator |
US20090297714A1 (en) * | 2008-06-02 | 2009-12-03 | Xerox Corporation | Flush pigment for solid inkjet ink |
US8123344B2 (en) | 2008-08-04 | 2012-02-28 | Xerox Corporation | Ink carriers containing surface modified nanoparticles, phase change inks including same, and methods for making same |
US8029861B2 (en) * | 2008-09-23 | 2011-10-04 | Xerox Corporation | Ink carriers containing low viscosity functionalized waxes, phase change inks including same, and methods for making same |
US8177897B2 (en) * | 2008-11-17 | 2012-05-15 | Xerox Corporation | Phase change inks containing graphene-based carbon allotrope colorants |
US8348409B2 (en) * | 2008-11-17 | 2013-01-08 | Xerox Corporation | Ink jet inks containing nanodiamond black colorants |
US7776147B1 (en) * | 2009-01-27 | 2010-08-17 | Xerox Corporation | Pigmented phase change inks with dispersant and synergist |
US7780774B2 (en) | 2009-01-27 | 2010-08-24 | Xerox Corporation | Method of making a pigmented phase change ink with dispersant and synergist |
US8118922B2 (en) | 2009-05-18 | 2012-02-21 | Xerox Corporation | Pigmented phase change inks containing low molecular weight quaternary ammonium salt dispersants |
US8101801B2 (en) | 2009-05-18 | 2012-01-24 | Xerox Corporation | Low molecular weight quaternary ammonium salt dispersants |
DE102010009379B4 (en) | 2010-02-26 | 2014-10-30 | Carl Zeiss Vision International Gmbh | Printing ink composition, process for printing and using the ink composition |
US8277032B2 (en) | 2010-08-05 | 2012-10-02 | Xerox Corporation | Acidic group-containing solid inks |
US8367020B2 (en) | 2010-08-05 | 2013-02-05 | Xerox Corporation | Hydroxyl group-containing solid inks |
US8449096B2 (en) * | 2010-12-06 | 2013-05-28 | Xerox Corporation | Five member ring stabilizers for quinacridone-type pigments in solid ink |
US8460451B2 (en) | 2011-02-23 | 2013-06-11 | 3D Systems, Inc. | Support material and applications thereof |
US8808437B2 (en) * | 2012-11-26 | 2014-08-19 | Xerox Corporation | Phase change inks containing quinacridone pigments and synergists |
US8721782B1 (en) | 2013-02-08 | 2014-05-13 | Xerox Corporation | Carbon black pigmented solid phase change ink formulations |
CN103205156B (en) * | 2013-04-11 | 2014-11-26 | 湖北师范学院 | Hot-melting veiled car line paste and preparation method thereof |
WO2015024953A1 (en) * | 2013-08-23 | 2015-02-26 | Sicpa Holding Sa | Anti-tampering composition and methods of use therefore |
EP3290485B1 (en) | 2014-09-18 | 2020-04-22 | Markem-Imaje Corporation | Ink compositions |
US9410051B2 (en) | 2014-09-25 | 2016-08-09 | Markem-Imaje Corporation | Hot melt inks |
US9944806B2 (en) | 2014-09-25 | 2018-04-17 | Markem-Imaje Corporation | Urethane compounds |
EP4127084A2 (en) | 2020-03-31 | 2023-02-08 | Dover Europe Sàrl | Ink compositions |
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US5592204A (en) | 1981-12-17 | 1997-01-07 | Dataproducts Corporation | Hot melt impulse ink jet ink with dispersed solid pigment in a hot melt vehicle |
US5350446A (en) | 1984-11-05 | 1994-09-27 | Dataproducts Corporation | Hot melt impulse ink jet ink with dispersed solid pigment in a hot melt vehicle |
US4814786A (en) | 1987-04-28 | 1989-03-21 | Spectra, Inc. | Hot melt ink supply system |
US5235350A (en) | 1990-01-22 | 1993-08-10 | Dataproducts Corporation | Pigmented semiconductive hot melt ink and ink jet apparatus employing same |
US5221335A (en) | 1990-05-23 | 1993-06-22 | Coates Electrographics Limited | Stabilized pigmented hot melt ink containing nitrogen-modified acrylate polymer as dispersion-stabilizer agent |
US5053079A (en) | 1990-05-23 | 1991-10-01 | Coates Electrographics Limited | Dispersed pigmented hot melt ink |
JPH04339871A (en) | 1991-05-16 | 1992-11-26 | Brother Ind Ltd | Hot-melt ink for ink jet printer |
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JPH06306319A (en) | 1993-04-26 | 1994-11-01 | Brother Ind Ltd | Hot-melt ink for ink-jet printer |
JP3000852B2 (en) | 1994-06-22 | 2000-01-17 | ブラザー工業株式会社 | Hot melt ink |
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AU5702196A (en) * | 1995-05-19 | 1996-11-29 | Chori Co. Ltd | Heat-fusible color ink |
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US5919839A (en) * | 1996-06-28 | 1999-07-06 | Tektronix, Inc. | Phase change ink formulation using an isocyanate-derived wax and a clear ink carrier base |
JPH1030072A (en) | 1996-07-15 | 1998-02-03 | Brother Ind Ltd | Hot-melt ink |
US6019829A (en) * | 1996-10-31 | 2000-02-01 | Mitsubishi Chemical Corporation | Carbon black aggregate |
US6153667A (en) | 1996-10-31 | 2000-11-28 | Pelikan Produktions, Ag | Hot melt ink |
WO1998050819A1 (en) | 1997-05-07 | 1998-11-12 | Seiko Epson Corporation | Display element and electronic clock |
JPH10316912A (en) | 1997-05-15 | 1998-12-02 | Brother Ind Ltd | Hot melt solid ink |
JPH10316914A (en) | 1997-05-15 | 1998-12-02 | Brother Ind Ltd | Hot-melt solid ink |
JPH10324832A (en) | 1997-05-23 | 1998-12-08 | Brother Ind Ltd | Hot melt ink |
JP3729310B2 (en) * | 1997-08-01 | 2005-12-21 | リコープリンティングシステムズ株式会社 | Hot melt ink composition for inkjet |
US6336965B1 (en) * | 1998-04-03 | 2002-01-08 | Cabot Corporation | Modified pigments having improved dispersing properties |
US6235098B1 (en) | 1998-06-26 | 2001-05-22 | Hitachi Koki Co., Ltd. | Hot-melt ink compositions for ink-jet printing |
CN100386390C (en) * | 1999-10-28 | 2008-05-07 | 卡伯特公司 | Ink jet inks, inks and other compositions containing colored pigments |
AU1353401A (en) * | 1999-10-28 | 2001-05-08 | Cabot Corporation | Ink jet inks, inks, and other compositions containing colored pigments |
-
2001
- 2001-12-31 US US10/032,132 patent/US6702884B2/en not_active Expired - Lifetime
-
2002
- 2002-12-27 AU AU2002360809A patent/AU2002360809A1/en not_active Abandoned
- 2002-12-27 WO PCT/US2002/041560 patent/WO2003057788A1/en not_active Application Discontinuation
- 2002-12-27 DE DE60239157T patent/DE60239157D1/en not_active Expired - Lifetime
- 2002-12-27 EP EP02796091A patent/EP1461393B1/en not_active Expired - Lifetime
Non-Patent Citations (1)
Title |
---|
No further relevant documents disclosed * |
Also Published As
Publication number | Publication date |
---|---|
EP1461393A1 (en) | 2004-09-29 |
WO2003057788A1 (en) | 2003-07-17 |
AU2002360809A1 (en) | 2003-07-24 |
DE60239157D1 (en) | 2011-03-24 |
US6702884B2 (en) | 2004-03-09 |
US20030127021A1 (en) | 2003-07-10 |
EP1461393B1 (en) | 2011-02-09 |
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